Updated Winter Classic Jersey Rankings Ahead of 2023-2024 Event
Joe YerdonDecember 31, 2023Updated Winter Classic Jersey Rankings Ahead of 2023-2024 Event

Ah yes, it's that time of year once again when we're ready to watch the NHL Winter Classic.
We also get to soak in the special uniforms for the Vegas Golden Knights and Seattle Kraken.
The two teams will face off from T-Mobile Park in Seattle on New Year's Day, and it's going to be cool as anything to see a pair of new teams get to participate in the NHL's annual big outdoor event.
While that's great, it gets us thinking about all the great (and not-so-great) Winter Classic jerseys from years past. As cool as the Kraken and Golden Knights jerseys might be (and they are, you haters), how they stack up with some of the gear we've seen each year since the event began in 2008 is debate-worthy. Who are we to sit back idly and not stoke the flames of such banter?
We're ranking the 10 best Winter Classic jerseys, and we're giving out more points for originality and subtle nods to nostalgia as opposed to just straight up ripping a page from the history books.
10. Boston Bruins (2023)

When you combine black and gold stripes and the Bruins' infamous "meth bear" on the front, you've got a winner of a jersey.
Sure, the Bruins have been in a pile of Winter Classics (three to be exact), but they've been able to mostly be original about things and have fun with it, too. Dusting off the wild-eyed bruin that resided on the shoulders of their jerseys through the 80s helped make this one a hit.
9. Montréal Canadiens (2016)

The Canadiens' old-style jersey with the globe on the sleeves to go with the bleu, blanc et rouge really made this jersey pop in 2016.
Getting an old fashioned "CH" on the front crest is what the iconic franchise needed to have in their first and only Winter Classic appearance to date, but the rest of it with the old style influence made this jersey sing.
8. New York Rangers (2018)

The Rangers have had a handful of Winter Classic appearances, and while their cream jerseys with the big shield in 2012 were really nice, it's their dark blue jerseys from the 2018 Winter Classic at Citi Field we're the biggest fans of.
This one still has the iconic Rangers shoulder stripes with "RANGERS" written diagonally, but the Rangers shield with "NY" makes this a great jersey. The Rangers have mostly done well with alternate jerseys in their history, but this one is among their best looks.
7. Philadelphia Flyers (2012)

When you think of the Flyers and jerseys, the thing that comes to mind first—apart from the superb logo—is the color orange. It's the color Bernie Parent and Bobby Clarke made famous (or infamous depending on your fandom) and established the Broad Street Bullies as a team to be feared and imitated (just look at the Syracuse Bulldogs in "Slap Shot").
So when Philly hosted the 2012 Winter Classic, the Flyers had to wear orange, and boy did they ever. These jerseys with the "keystone" captain and alternate captain patches were awesome, and they helped the Flyers stand out brightly at Citizens Bank Park.
6. Dallas Stars (2020)

When the Dallas Stars hosted the 2020 Winter Classic at the Cotton Bowl, they wanted to ensure the world would know that Dallas' hockey history ran deep and leaned into the city's hockey history for this look.
Everything is bigger in Texas, they say, and the letter "D" on this one was definitely big. This green sweater made for a great look in a Winter Classic that sometimes gets forgotten about.
5. Pittsburgh Penguins (2011)

Pittsburgh Penguins fans swear up and down that I'm trolling them by picking this jersey as one of the best, but let's be real: It's awesome despite the negative connections to it because of Sidney Crosby's injury in that game and all that.
This look with the perfect circular Penguins logo with the skating penguin wearing a scarf on the deep, dark blue jersey with baby blue stripes—part of the team's color base when they began play in 1967—called back to the franchise's inception but provided a gorgeous (yet now haunted) look.
4. Boston Bruins (2010)

This golden Bruins throwback look from the 2010 Winter Classic is an all-time great. Not just because they were bold enough to go with a bright yellow jersey and an old school logo, but seeing this look on the ice at Fenway Park with a team ready to hit their stride as one of the best in the NHL (they won the Stanley Cup a year later) was just awesome.
This jersey, like most Winter Classic jerseys, didn't have much of a shelf life, and that's too bad, because it's incredible.
3. Toronto Maple Leafs (2014)

The 2014 Winter Classic from Michigan Stadium in Ann Arbor between the Detroit Red Wings and Toronto Maple Leafs was perhaps the best looking of them all.
It was a color-on-color game in front of more than 100,000 fans in what turned into a snow globe atmosphere in bitterly cold temperatures. The Maple Leafs jerseys for this game were as good as they get.
The Leafs had stripes upon stripes on the sleeves and the old-time style Maple Leafs logo on the front was can't-miss. A truly great look overall.
2. Seattle Kraken (2024)

The Kraken jerseys for this year's Winter Classic are essentially what everyone has been clamoring to see since it was announced Seattle was getting an NHL franchise.
The big red Kraken logo on the front with "KRAKEN" spelled out on the sea monster letter "S" calls back to the days of the Seattle Metropolitans, and it's a great look! It's also one the owner of the Metropolitans trademark seems to think hearkens a bit too closely to the original to the point of filing a lawsuit about it.
Legal stuff aside, this jersey absolutely rocks and should look great during the game on January 1.
1. Detroit Red Wings (2014)

We told you the 2014 Winter Classic looked great, and having both teams in the top three of our ranking shouldn't surprise you. That it's the Red Wings coming away with the No. 1 spot here also shouldn't surprise you, because look at those jerseys.
It's simple, it's throwback-looking while not being a direct throwback and it provided something that was slightly different than what the Wings have worn for ages in the NHL. Watching Henrik Zetterberg and Pavel Datsyuk fly around the ice at the Big House in these helped make it even more special.
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